3 Situations When You’ll Need to Confront Your Boss (and Exactly What to Say When You Do)

March 27, 2018

So, you need to confront your boss. Are your palms getting sweaty at the thought?

You aren’t alone. Needing to assert yourself to your manager—ideally, in a way that doesn’t make you come off like a pushy know-it-all—is a tricky thing.

You already have the basics covered. You know you should double-check your facts, try to problem-solve yourself, and get your ducks in a row before you stick your neck out and potentially damage your relationship with your supervisor.

But, you’ve already done all of that, and there’s no getting around this fact: You absolutely need to have that dreaded (and hopefully not heated) conversation with your boss.

Now you’re met with the even tougher challenge of figuring out exactly what you should say. Fortunately, I’m here to help. Here are three common scenarios when you’ll need to stand your ground with your superior—as well as how to get that conversation rolling.

Ah, that awkward moment when you know you’re right and that your boss is completely wrong.

Perhaps your manager keeps citing an incorrect statistic or stubbornly maintains that his approach to a specific project is the best way to go. But, you? You firmly disagree. You’re completely confident that you’re in the right here.

You’re eager to sway him over to your way of thinking (you know, the right way), without coming off as condescending or cocky.

“I Thought That Same Thing, But…”

One of the best ways to stick to your guns without majorly bruising your boss’ ego? By grouping yourself in with him.

A phrase like this one demonstrates sympathy by making it clear that you had that same thought process, but eventually went another way when you uncovered an important piece of information—which you should share at this point in time. Even if it is a little white lie, it’s a great way to assert yourself in a way that’s still supportive and cooperative.

“I Can Show You Where I’m Getting This Answer…”

If you have facts on your side, there’s nothing wrong with opening your supervisor’s eyes to what is leading you to feel the way you do.

When you’re standing firm that you have the right answer in this situation, walk your boss through exactly how you arrived at that conclusion. He’ll have a tough time arguing with solid proof.

You have way to much work on your plate and are spread way too thin, meaning you need to loop your boss in on the fact that you’re feeling overworked so that she can hopefully help you reach a more realistic workload.

But, you’re afraid that the whole exchange will just make you look like a complainer who can’t get anything done. Have no fear—that’s exactly why these two phrases are so helpful.

“I’m Trying to Prioritize My Tasks…”

You want to make it clear that you aren’t trying to shirk responsibilities altogether. Instead, you’re attempting to ensure that you have the necessary time and energy for the things that your supervisor views as priorities.

A phrase like this one is great, as it can segue into a request for help to sort through your existing to-dos and zone in on the most important ones. It turns the conversation into a collaborative effort to order your workload, rather than a major complaining session.

“Because [Project] Is Demanding So Much of My Time and Attention…”

If you’re worried about presenting yourself like a good-for-nothing, lazy employee, it’s a smart strategy to direct your boss’ attention to something major that you’re working on.

When there’s a larger project that’s demanding the majority of your resources, point that out to your manager so that you two can have a conversation about any less-pressing tasks that could be delegated or eliminated for now.

You have a deadline looming over your head. The only problem? You’re stuck at a standstill while you wait on something that you need from your superior.

Cringe, right? Needing to manage up can be a delicate situation to cope with. You need your boss to hold up his end of the deal. But, you also don’t want to seem like you’re telling him what to do.

“I Know You Have a Lot on Your Plate…”

One of the best methods for broaching this subject in a gentle way is to start by recognizing how busy your manager is. After you’ve acknowledged his packed schedule, you can ask when you can expect to receive that deliverable you’re waiting for.

I know, it can make you feel like a bit of a brownnoser. But, if you’re concerned about coming off like a pesky micromanager, it’s a great way to segue into the conversation without pointing fingers and assigning blame.

“Do You Think I’ll Still Be Able to Have This Project Completed By [Date]?”

Because leaders are often juggling numerous different things at once, it’s easy for them to miss the forest for the trees. They don’t realize how their delay could impact the overall assignment.

When your boss is really lagging behind, use a question like this one to remind her of the deadline for your entire project—rather than just her piece of the puzzle.

Whether it was promised to a client by a specific date or you have other members in the organization waiting on its completion, nudging your boss with the firm deadline (rather than a wishy-washy end date of when you’d hoped she’d be finished) will hopefully give her a push in the right direction.

Needing to confront your boss is usually enough to make your stomach do flips and your mouth go dry. But, chances are, you’re going to need to do it every now and then.

Fortunately, there are a few phrases you can use to approach that conversation in a way that presents you as poised and put-together—rather than pushy and patronizing.

When you find yourself in one of the above situations? Give these a try and prepare for a productive discussion (no tears, screaming, or shaky knees required).